Photoaddition reactions of acetylene and butadiyne derivatives to benzodithiophene

Journal of Organic Chemistry

Volumn 68, Issue 21, 2003, Pages 8258-8260

  Wex, Brigitte ^a   Kaafarani, Bilal R ^b   Oliver, Allen G ^c   Krause Bauer, Jeanette A ^d   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC HYDROCARBONS; DERIVATIVES; PHOTOCHEMICAL REACTIONS; SUBSTITUTION REACTIONS;

PHOTOADDITION REACTIONS;

ACETYLENE;

ACETYLENE DERIVATIVE; ACETYLENEDICARBOXYLATE; AROMATIC COMPOUND; BENZO[1,2 B, 4,5, B']DITHIOPHENE; BENZODITHIOPHENE; BENZOTHIOPHENE DERIVATIVE; BUTADIYNE DERIVATIVE; BUTANE; CARBOXYLIC ACID DERIVATIVE; CYCLOBUTA[B]THIENO[2,3 F][1]BENZOTHIOPHENE; CYCLOBUTANE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION KINETICS; CYCLOADDITION; PHOTOADDITION REACTION; PHOTOCHEMISTRY; PRODUCTIVITY; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 0142121711     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034742x     Document Type: Article

References (37)

1. This paper is dedicated to Professor Dr. J. W. Neckers on the occasion of his 101st birthday.
2. Wynberg, H. Acc. Chem. Res. 1971, 4, 65-73.
3. Pomerantz, M.; Wang, J. P.; Seong, S.; Starkey, K. P.; Nguyen, L.; Marynick, D. S. Macromolecules 1994, 27, 7478.
4. Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J.; Dodabalapur, A. Adv. Mater. 1997, 9, 36.
5. Yamamoto, R. Jpn. Kokai Tokkyo Koho JP 11322906 A2, 1999.
6. Wynberg, H.; Kellogg, R. M.; van Driel, H.; Beekhuis, G. E. J. Am. Chem. Soc. 1966, 88, 5047.
7. Kuhn, H. J.; Gollnick, K. Chem. Ber. 1973, 106, 674.
8. Geerts, Y.; Klärner, G.; Müllen, K. Hydrocarbon Oligomers. In Electronic Materials: The Oligomer Approach. Müllen, K., Wegner, G. Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 1 and references therein.
9. Campbell, S. J.; Kelly, D. C.; Peacock, T. E. Aust. J. Chem. 1989, 42, 479.
10. Reinhoudt, D. N. Adv. Heterocycl. Chem. 1977, 21, 253.
11. Dopper, J. H.; Neckers, D. C. J. Org. Chem. 1971, 36, 3755.
12. Neckers, D. C.; Dopper, J. H.; Wynberg, H. Tetrahedron Lett. 1969, 2913.
13. Ditto, S. R.; Davis, P. D.; Neckers, D. C. Tetrahedron Lett. 1981, 22, 521.
14. MS m/z (%): 300 (92) [M - 32], 268 (100), 254 (45), 182 (53), 170 (36), 138 (31).
15. Hofman, H.; Westernacher, H.; Haberstroh, H.-J. Chem. Ber. 1969, 102, 2595.
16. We are currently investigating this observation.
17. (a) Arnold, D. R.; Chang, Y. C. J. Heterocycl. Chem. 1971, 8, 1097.
18. (b) Serve, M. P.; Rosenberg, H. M. J. Org. Chem. 1970, 35, 1237.
19. (c) Owsley, D. C.; Bloomfield, J. J. J. Am. Chem. Soc. 1971, 93, 782.
20. (a) Shim, S. C.; Lee, T. S.; Lee, S. J. J. Org. Chem. 1990, 55, 4544.
21. (b) Shim, S. C.; Kim, S. S. Bull. Korean Chem. Soc. 1985, 3, 153.
22. (c) Chung, C. B.; Kim, G.-S.; Kwon, J. H.; Shim, S. C. Bull. Korean Chem. Soc. 1993, 14, 506.
23. (a) Lee, S. J.; Shim, S. C. Tetrahedron Lett. 1990, 31, 6197.
24. (b) Shim, S. C.; Kim, S. S. Tetrahedron Lett. 1985, 765.
25. Shim, S. C.; Lee, S. J.; Kwon, J. H. Chem. Lett. 1991, 1767.
26. (a) Salah, B. Aust. J. Chem. 1976, 29, 531.
27. (b) Bevan, W. I. J. Chem. Soc., Dalton Trans. 1974, 2302.
28. Rodriguez, J. G.; Martin-Villamil, R.; Cano, F. H.; Fonseca, I. J. Chem. Soc., Perkin. Trans. 1 1997, 709.
29. Kitamura, T.; Lee, C. H.; Taniguchi, Y.; Fujiwara, Y. J. Am. Chem. Soc. 1997, 119, 619.
30. Birks, J. B. Photophysics of Aromatic Molecules; New York: Wiley, 1970; p 403.
31. Ryashentseva, M. A.; Belanova, E. P.; Minachev, Kh. M.; Polosin, V. M.; Bodganov, V. S. Bull. Acad. Sci. USSR Div. Chem. Sci. 1988, 37, 2579.
32. Nagano, Y.; Ikoma, T.; Akiyama, K.; Tero-Kubota, S. J. Chem. Phys. 2001, 114, 1775.
33. ex = 302 nm) were recorded in ethyl iodide/ethanol/isopentane (1/2/1) at 77 K (liquid nitrogen) and a sample concentration of 17.6 mM.
34. Nagano, Y.; Ikoma, T.; Akiyama, K.; Tero-Kubota, S. J. Phys. Chem. 1998, 102, 5769-5774.
35. Baughman, R. H. J. Appl. Phys. 1972, 43, 4362-4370.
36. Neckers, D. C.; Wagenaar, F. L.; Hauenstein, D.; Jacobson, R. A. J. Org. Chem. 1983, 48, 1725.
37. Crystallographic data are deposited at the Cambridge Crystallographic Data Center (CCDC no. 211794).